Middleburg Vacation Packages

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Your Middleburg Vacation

With every last detail planned before you go away, our Middleburg vacation packages mean you can focus more on letting the good times roll. Whether you stay in the neighborhood of Stone Ridge, which is good for walking, or someplace else in town, this lively city promises a world of discoveries. You'll want to take in the sights during your trip to Middleburg. Carve out some time for major attractions such as Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. A few quick clicks is all it takes to put together the ultimate Middleburg vacation on Expedia.

Top Middleburg Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Price was CA $1,123, price is now CA $752 per person
CA $752
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
7.6/10 Good! (1,027 reviews)
The check in was easy and the room was amazing. I loved the shower and bathroom. Staff were friendly and helpful.

Reviewed on Mar 29, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $1,444, price is now CA $1,039 per person
CA $1,039
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.6/10 Excellent! (1,008 reviews)
Clean. Friendly staff. Great location. Room was clean. Bed was comfy. Bar and restaurant on site. My only complaint was the shower head wasn’t the best and the air/heat was loud. But that is being picky. Would definitely stay again.

Reviewed on Mar 30, 2026

Hilton Arlington National Landing

Hilton Arlington National Landing

4 out of 5
Crystal City
Price was CA $1,110, price is now CA $829 per person
CA $829
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.8/10 Excellent! (753 reviews)
Great service Great Hotel

Reviewed on Mar 29, 2026

Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
Price was CA $1,114, price is now CA $838 per person
CA $838
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (IAD)
8.8/10 Excellent! (1,000 reviews)
The staff was excellent and we enjoyed our stay and breakfast. The location was excellent. However the rooms show degradation, for example there are white paints dripped on the bathroom wood floor, which is simply a poor clean up process after remodeling.

Reviewed on Mar 29, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was CA $1,165, price is now CA $885 per person
CA $885
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9/10 Wonderful! (1,153 reviews)
Really nice hotel and near the main turist attractions

Reviewed on Apr 1, 2026

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Middleburg Hotel Deals

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
The price is CA $811 per night from Apr 6 to Apr 7
CA $811
CA $996 total
Apr 6 - Apr 7
includes taxes & fees
9.2/10 Wonderful! (388 reviews)
We visited the Salamander Resort and Spa this spring for a quick trip. The hotel was beautiful and the staff was wonderful. Thank you for a great trip!

Reviewed on Mar 25, 2026

Salamander Resort And Spa
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
The price is CA $383 per night from Apr 5 to Apr 6
CA $383
CA $552 total
Apr 5 - Apr 6
includes taxes & fees
10/10 Exceptional! (57 reviews)
Tim is a great host. The cottage was clean, comfortable and perfectly located. Perfect place to stay for a weekend getaway to Middleburg!

Reviewed on Mar 1, 2026

18th Century Stone Cottage minutes from historic Middleburg
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
The price is CA $433 per night from Apr 12 to Apr 13
CA $433
CA $493 total
Apr 12 - Apr 13
includes taxes & fees
9.6/10 Exceptional! (429 reviews)
Parking was secure, staff was really friendly, thermostat was not in the room and we were unable to adjust the temperature in the room

Reviewed on Mar 23, 2026

The Red Fox Inn & Tavern
See all 976 properties in Middleburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Discover the most popular places to visit in Middleburg

Cana Vineyards and Winery

You can enjoy a tasting or tour at Cana Vineyards and Winery during your travels to Dover. While in this trendy area, you can savor the top-notch restaurants.

Cana Vineyards and Winery

The Byrne Gallery

You can spend an afternoon exploring the galleries in The Byrne Gallery during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

The Byrne Gallery

What to do in Middleburg

Luxe Day Trip: 3 VA Wineries & Optional Tasting-Inclusive Upgrade

3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade

CA $165
per adult
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
See all activities in Middleburg

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.